Jockstrap Stories

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Infinite Scroll

Painful Pleasure

by AnnaKena on Sep 17, 2017
BDSM

They pulled up in front of Club Rosas. A cool breeze was blowing, it was nearly 22:00 and they were dot on time for their appointment. Bob and Julie walked up to the heavy oak door and she pressed the bell. Almost instantly, the door opened and an attractive man in his early forties smiled at her. She smiled back. "Hello, please come in. Julie and Bob, fi...

Dolores Park after Dark

by realpussyboy on Sep 12, 2017
Transsexuals & Crossdressers

When we were walking through Pride earlier, he mentioned that he thought the men in utility kilts were hot and, more significantly, that he thought I would look hot in a utili-kilt. The he, in this case, was Carter, the hot guy I hoped would eventually become my boyfriend. And this outing to Pride was our fourth date. At first I scoffed at the idea of wearin...

White Boy Swagg

by puzziboi on Mar 23, 2020
Transgender & Crossdressers

"Y'all tell Gigi and Big Dad bye," instructed the thirty-one year old father of two. "Bye, bye," said the older one - a girl of four. The younger kid, a boy aged two, began to pout. "Come on now, Maverick. Stop actin'. You know you're goin' to a birthday party,' ' Josh Myers reminded his son. "It's okay, Mav! Gigi will come see you later," Lori Myers att...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

Becoming a Cum Dump Ch. 08

by plyasian on Sep 14, 2017
BDSM

BEEP! BEEP! I rolled over and pulled out my phone. 6:45am. Tuesday, October 6th. I quickly hopped into the shower where I did a once over of my body. My hair had grown back a little so I quickly shaved it off. When I finished, I headed back to my room to figure what I was going to wear. Shit what do I wear. It was easy when I had Thomas making the decisio...

Seeing My Ex-Husband's Big Cock

by Cute_Little_Muffin on Jul 14, 2020
Exhibitionist & Voyeur

I: An eyeful at the barbeque: Before this lockdown caused by the pesky Covid19, my son had persuaded me to go along with him to watch his Dad play rugby. It was a fab chance to make a picnic and watching big, strong, masculine men sweating and grunting as they displayed their masculinity wasn't too much of a chore. As the field doesn't have any facilities...

Sensitivity Training Can Mean a Lot Ch. 07

by JimAner on Sep 18, 2017
Fetish

Sensitivity Training can mean a lot: Part 7 Meanwhile back home. While this can be a stand-alone story, still it is a chapter in the larger story. It takes place back home while Beercan (AKA Jason) is spending his first two weeks at the Institute. Beercan was sent Sensitivity Institute of America because he had sexually harassed one of his employees. His b...

Frontier Incident

by smilodonwriter on Sep 1, 2017
Humor & Satire

To the Senate and People of Rome from Q. Cassius Sextus, Senior Tribune, Legio XIV, Hale! I am commanded by Didius Claudius Meritus, Governor of Phrygia to offer the following report into the causes of the late unpleasantness in the city of Atarbraxis, since renamed Pentium. I know you will be all familiar with the facts regarding the results of the rioting...

Return to Funnel Ch. 02

by a real jrkoff on Sep 17, 2017
Fetish

Abigail Moran had retrieved the black plastic funnel from the doghouse and returned it to Ms. Crenshaw. She watched, fascinated as the woman forced it into her son’s mouth and buckled the connecting straps about his head so he would be made to keep it in place. Then she took up the semen filled dogdish and brought it up near his face. “Now Thomas. Be a good...

Molding Clay Ch. 03

by KalePond13 on Jun 9, 2020
BDSM

After the almost accident in the weight room, Coach decided that was more than enough exercise for the day. They were now both in the locker room again, their weight training done, and it seemed neither really wanted to talk about what had just conspired a few minutes ago. Clay's head was still swimming a bit, partly from exhaustion, partly from the whiff...